Synthesis, properties, and redox behavior of tetracyanobutadiene and dicyanoquinodimethane chromophores bearing two azulenyl substituents

Taku Shoji, Mitsuhisa Maruyama, Erika Shimomura, Akifumi Maruyama, Shunji Ito, Tetsuo Okujima, Kozo Toyota, Noboru Morita

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

Acetylene derivatives with an azulenyl group at both terminals have been prepared by palladium-catalyzed alkynylation under Sonogashira-Hagihara conditions. These alkynes reacted with tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane in a formal [2 + 2] cycloaddition- retroelectrocyclization reaction to afford the corresponding new tetracyanobutadienes (TCBDs) and dicyanoquinodimethanes (DCNQs), respectively, in excellent yields. Intramolecular CT absorption bands were found in the UV-vis spectra of the novel chromophores, and CV and DPV showed that they exhibited a reversible two-stage reduction wave, due to the electrochemical reduction of TCBD and DCNQ moieties. Color changes were also observed during the electrochemical reduction.

Original languageEnglish
Pages (from-to)12513-12524
Number of pages12
JournalJournal of Organic Chemistry
Volume78
Issue number24
DOIs
Publication statusPublished - 2013 Dec 20

ASJC Scopus subject areas

  • Organic Chemistry

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